Amino acids chemical stability submitted to solid state irradiation: the case study of leucine, isoleucine and valine

Cherubini, Cristina; Ursini, Ornella

doi:10.1186/s40064-015-1332-9

Cited by 14 publications

(7 citation statements)

References 34 publications

(34 reference statements)

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“…However, the present work reveals that there are photochemical channels for stereoinversion, which can be initiated by UV radiation. This is also in line with radioracemization study of Leucine by Cherubini and Ursini, where a slow radio‐racemization of Leucine has been reported, because the stereoinversion is not a barrierless process even in the excited state. However, under such conditions, dissociation of the species involved becomes extremely significant which is further analysed below.…”

Section: Resultssupporting

confidence: 89%

“…Nevertheless, both the previous experimental studies reported the high temperature above 500 K to be the dissociating temperature for Leucine. Apart from this, a radio‐stability study of Leucine also reported that up to 70 % of Leucine is preserved in high γ radiation of 3.2MGy. This is important since the thermochemical and kinetic analysis in the present work predicts stereoinversion routes to be feasible at temperatures between 100–500 K. Notably, under such conditions, photochemically initiated stereoinversion, via route 2b, can predominantly occur over the dissociation.…”

Section: Resultsmentioning

confidence: 95%

“…The enantio‐enrichment of Leucine has been reported in absolute asymmetric photochemical reactions through synchrotron radiations of circular polarization . Besides this, the radio‐racemization via non‐polarized light by irradiating Leucine with gamma radiation has also been investigated by Cherubini et al . Such photochemical routes, however, involve excited‐state PES, which though are quite difficult to explore.…”

Section: Introductionmentioning

confidence: 99%

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Extra‐Terrestrial Gas‐Phase Stereoinversion in Amino Acid Leucine: Thermal and Photochemical Channels

Rani

Vikas

2020

ChemPhysChem

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Enantiomeric‐excess of the left‐handed enantiomer of proteinogenic amino acids has been reported in the meteoritic samples of carbonaceous chondrites. Such chiral‐bias is recently being believed due to the removal of right‐handed enantiomer through its selective destruction by circularly polarized ultraviolet (UV) radiations in interstellar space. The present work through quantum mechanical computations explores various thermal and photochemical channels for stereoinversion in proteinogenic amino acid Leucine, under the gas‐phase conditions akin to different temperature zones of interstellar medium (ISM). A thermochemical and kinetic analysis for the feasibility of the proposed channels is also carried out in different regions of ISM. The initiation of stereoinversion along all the ground‐state thermal channels is found to be restricted by a very high energy barrier which, however, is proposed to be substantially reduced if the initial step proceeds via an excited‐state. This work reveals that the stereoinversion in Leucine is quite feasible in ISM, provided it is initiated photochemically by UV radiations, which are abundant in ISM.

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Section: Resultssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

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Extra‐Terrestrial Gas‐Phase Stereoinversion in Amino Acid Leucine: Thermal and Photochemical Channels

Rani

Vikas

2020

ChemPhysChem

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“…Calculations indicate that in primitive Earth, 40 K decay reached up to around 0.29 mGy per year (Ernst, 1983), which emitted γ and β radiation (Dymek and Klein, 1988; Draganić, 2005). On the other hand, it has been estimated that the energy deposited by the decay of radionuclides in comets, asteroids and meteorites waste about 14 × 10 9 mGy over 4.6 × 10 9 years (Cataldo et al ., 2011; Cherubini and Ursini, 2015). The search related to the interactions between ionizing radiation and organic substances, such as formaldehyde, is essential for understanding certain steps in chemical evolution and the origin of life.…”

Section: Introductionmentioning

confidence: 99%

Stability of aqueous formaldehyde under γ irradiation: prebiotic relevance

López-Islas

Colín-García

Negrón‐Mendoza

2018

International Journal of Astrobiology

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Formaldehyde is a precursor of sugars, which are compounds essential in all forms of life and a necessary molecule for prebiotic processes. This work focuses on evaluating the stability of formaldehyde exposed to a high radiation field simulating prebiotic conditions on primitive Earth, such as the ocean or shallow waters. Formaldehyde may have been formed from reactions in the atmosphere and from rainout processes reached water bodies. In our experiments, we employed γ radiation and found that formaldehyde was labile towards radiation and decomposed even at low irradiation doses due to the fact that aldehyde/hydrate groups present in formaldehyde structure are very reactive under irradiation. However, after exposing this molecule to several doses of irradiation, we detected the formation of formic acid and glycolaldehyde – both of which are of prebiotic interest. We also observed formaldehyde regeneration by one of its radiolytic products: formic acid.

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“…53 Many studies have been performed to investigate how organic compounds have formed and survived in a (simulated) harsh cosmic environment. [54][55][56][57][58] Most of these studies focus on the effect that ionizing radiation has on the chirality of amino acids. These studies provide data explaining the non-racemic mixtures of amino acids observed in meteorites.…”

Section: Introductionmentioning

confidence: 99%

Investigating Hydrothermal and Radiation Effects on Nitrogen Heterocycles Relevant to Meteorite Parent Bodies

Hammer¹

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supporting this research and my graduate studies. I would also like to thank the ELSI (Earth-Life Science Institute) Origins Network for supporting this research. I would especially like to thank Dr. Henderson (Jim) Cleaves who acted as my guide and colleague while conducting research at the Tokyo Institute of Technology in Japan. I consider him a friend now. In addition, I want to thank Ruiqin Yi, Mayuko Nakagawa, and Kyoko Akiyama for their hard work and their help guiding me through working in a foreign laboratory. Thank you to Dr. Aaron Burton and Dr. Darren Locke at NASA Johnson Space Center for analyzing NH4CN polymers by TMAH GC-MS and providing the data for me to analyze. I would like to thank Dr. Karen Smith for reading and editing my thesis. Finally, I would like to thank the faculty and staff in the Department of Chemistry and Biochemistry including those on my thesis committee who helped me throughout graduate school. I'm proud to say Boise State University is my alma mater for both my B.S. and M.S. degrees in Chemistry. Prof. Callahan…you know what you did. I blame all this-the research, the travel, the conferences, continuing to pursue a doctorate, and this dissertation ON YOU!!! vi ABSTRACT Organic compounds in meteorites were likely transformed by a variety of processes on the asteroid parent body including aqueous, thermal, and radiolytic alteration. Previous studies have identified a suite of purine nitrogen heterocycles in carbonaceous chondrites (a class of meteorites) and determined that their likely origin was due to cyanide chemistry. The thesis research described here consisted of two parts: investigating thermal effects on aqueous ammonium cyanide reactions and the production/survivability of organics (Chapter 2) and investigating gamma radiation effects on purine nitrogen heterocycles to understand how prolonged radiation exposure influenced the distribution and abundance of nitrogen heterocycles measured in meteorites today (Chapter 3). A temperature study of 1 M ammonium cyanide was conducted from room temperature to 200 °C (temperatures similar to the aqueous alteration of some carbonaceous chondrites) using a high-pressure reaction vessel. The resulting liquid supernatant and water insoluble cyanide (hetero)polymer were isolated and analyzed by attenuated total reflectance Fourier transform infrared spectroscopy and thermochemolysis gas chromatography-mass spectrometry using tetramethylammonium hydroxide or highperformance liquid chromatography with UV detection (HPLC-UV). A strong correlation was observed between thermochemolysis products of cyanide polymers and the initial reaction temperature-production of aromatic compounds increases and nitrogen containing compounds decrease with respect to increasing reaction temperature. The data presented in this thesis suggests that the polymer may be a less efficient source of nitrogen vii heterocycles when produced at high temperatures. HPLC-UV analysis showed that the supernatant of heated NH4CN reactions is a complex mixture containing m...

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Amino acids chemical stability submitted to solid state irradiation: the case study of leucine, isoleucine and valine

Cited by 14 publications

References 34 publications

Extra‐Terrestrial Gas‐Phase Stereoinversion in Amino Acid Leucine: Thermal and Photochemical Channels

Extra‐Terrestrial Gas‐Phase Stereoinversion in Amino Acid Leucine: Thermal and Photochemical Channels

Stability of aqueous formaldehyde under γ irradiation: prebiotic relevance

Investigating Hydrothermal and Radiation Effects on Nitrogen Heterocycles Relevant to Meteorite Parent Bodies

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